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Volume 83, Issue 8
Displaying 1-20 of 20 articles from this issue
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Reactions of Diketene with Isonicotinic Acid HydrazideTetsuzo Kato, Hiroshi Yamanaka, Fumiko Hamaguchi1963 Volume 83 Issue 8 Pages 741-744
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIsonicotinic acid hydrazide (INAH) affords its acetoacetate (IV), when reacted with diketene. IV gives isonicotinopiperidide and 3-methyl-2-pyrazolin-5-one (VII) in the presence of piperidine in ethanol solution, and it also produces VII and isonicotinc acid in the presence of pyridine in acetic acid solution. IV affords INAH and 1-phenyl-3-methyl-2-pyrazolin-5-one (II), when reacted with phersylhydrazine and it also produces VII and 1, 1-diisonicotinoylhydrazine (VIII) in the reaction with INAH. However the cyclization reaction of isonicotinoylpyrazolone (V or VI) was unsuccessful. IV is hydrolyzed into VIII, VII and acetone, emitting carbon dioxide gas. On the other hand, the hydrolysis of IV, after the benzylation, gave 3-methyl-4-benzyl-2-pyrazolin-5-one and isonicotinic acid. The reaction mechanisms is discussed in this report.View full abstractDownload PDF (628K) -
7-Aminopyrazolo [1, 5-a] pyrimidine and its Methyl Substituted DerivativesAkira Takamizawa, Yoshio Hamashima, Sadao Hayashi, Ryonosuke Kido1963 Volume 83 Issue 8 Pages 745-752
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSBased upon the fact that 7-amino-3, 6-dimethylpyrazoio[1, 5-a]pyrimidirie (XIII) possesses effective antipyretic and analgetic action, 14 methyl substitutes of 7-aminopyrazolo[1, 5-a]-pyrimidine in its nuclei were synthesized.
With 5-aminopyrazoles (VII-X), 2-methyl-3-ethoxy-3-methoxypropionitrile (I) was reacted to give 6-methyl compounds (XI-XIV), acetoacetonitrile (III) was reacted to give 5-methyl derivatives (XV-XVIII), 2-acetopropionitrile (IV) to 5, 6-dimethyl derivatives (XIX-XXII), and ethyl ethoxymethylenecyanoacetate (V) to 6-ethoxycarbonyl derivatives (XXVII-XXX). In this connection, the cyclization with V in both acidic and alkaline media, and the saponification of XXVII-XXX were investigated. The thermal decomposition of XXXV-XXXVIII produced decarboxyl compounds (XXXIX-XLII) easily. Another synthetic method of XLII was also studied.View full abstractDownload PDF (1113K) -
Susumu Umemoto, Shinsuke Ose, Hideji Takamatsu1963 Volume 83 Issue 8 Pages 753-756
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn order to reduce the side effect of N-phenylacetylureas, hitherto used as anticonvulsants, 1-acyl-3-phenylacetylureas were prepared by acylation of N-phenylacetylureas or by the reaction of acylisocyanates and acylamides. Of the compounds synthesized, 1-acetyl-3-(1-ethylphenylacetyl)urea was found to be a convulsant with small side effect.View full abstractDownload PDF (672K) -
Yononin and Tokoronin, New Steroid Saponins in the Rhizome of Dioscorea Tokoro MAKINOToshio Kawasaki, Tatsuo Yamauchi1963 Volume 83 Issue 8 Pages 757-760
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIt is known that, among the sapogenins contained in Dioscorea Tokoro MAKINO, majority of yonogenin and tokorogenin are present in a free state in the aerial part. Two kinds of new steroidal saponins with yonogenin and tokorogenin as their aglycones were isolated from the water-insoluble saponin fraction of the rhizome of this plant. These saponins are yonogenin α-L-arabinoside (I), m. p. 238-240° (decomp.), [α]D15-14.5°, and tokorogenin α-L-arabinoside (II), m. p. 270-274° (decomp.), [α]D15-10.6°, which were respectively named yononin and tokoronin.View full abstractDownload PDF (643K) -
Structure of Trilobine and Isotrilobine. (16). Structure of TrilobineMasao Tomita, Hiroshi Furukawa1963 Volume 83 Issue 8 Pages 760-763
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe structure of trilobine was reported by Inubushi and Nomura as the formula (I) from the cleavage reaction of its N-acetyl compound with metallic sodium in liquid ammonia. The antipodal isotrilobine (II) was synthesized from dlhydroepistephanine (V) by the present writers.
In the present series of work, O-methylanhydrodemethyl-N-ethyl-dihydroepistephanine (X) was synthesized from N-ethyldihydroepistephanine (VII) by a similar method. X came as a picrate of m.p. 194-195°, [α]D-283.1° (acetone), C37H38O5N2⋅2C6H3O7N3⋅1 1/2H2O. By comparison with the picrate, m.p. 193-195°, [α]D+283.8° (acetone), C37H38O5N2⋅2C6H3O7N3⋅1 1/2H2O, of the N-ethyl compound (III) from natural trilobine (I), X was found to be its antipode (cf. Table I). Consequently, the structure of trilobine was reaffirmed as I by synthesis.View full abstractDownload PDF (574K) -
Masao Tomita, Mutsuo Kozuka, Etsuko Nakagawa, Yukiko Mitsunori1963 Volume 83 Issue 8 Pages 763-766
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSFrom the barks and woods of Laurus nobilis LINN., Japanese name “Gekkeiju” cultivated in Japan, actinodaphnine (III) and a new secondary aporphine-type base, launobine, C18H17O4N, m. p. 214-215° (decomp.), [α]D21+192.7°, were isolated and the structure of the latter has been certified to be VII.View full abstractDownload PDF (695K) -
Synthesis and Antifungal Activity of Thiocyanatopyridazine DerivativesJiro Kinugawa, Michihiko Ochiai, Hiroichi Yamamoto1963 Volume 83 Issue 8 Pages 767-771
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA new kind of thiocyanatopyridazine derivatives were synthesized and their antifungal activities were tested. 3-Halogeno-6-thiocyanatopyridazine, 4-thiocyanato-3, 6-dichloropyridazine were found to show the remarkable activity.View full abstractDownload PDF (726K) -
Syntheses and Antibacterial Activities of 2-(5-Nitro-2-furyl) vinyl HeterocyclicsKoji Miura, Tomiji Oohashi, Sumie Matsuda, Yoshiko Igarashi1963 Volume 83 Issue 8 Pages 771-777
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA total of 28 kinds of Panfuran-type compounds, in which the nitrofuran and heterocyclic rings are connected through one double bond, were prepared and their antibacterial action was tested with Streptococcus haemolyticus, Staphylococcus aureus, Escherichia coli, Shigella flexineri, and Bacillus subtilis. The quinoline compounds were found to be most effect as a chemotherapeutic and acetamidoquinoline derivative showed the most marked effect, inhibiting bacterial growth of Bacillus subtilis in a very dilute solution of ca. 2, 000, 000, 000 dilution.View full abstractDownload PDF (557K) -
Especially Comparative Studies on the Chemotherapeutic Effect of 2-Amino-5-[2-(5-nitro-2-furyl) vinyl]-1, 3, 4-thiadiazole and Sulfamethylthiadiazole in Mice Infected with StreptococcusKoji Miura, Masao Ikeda, Yoshiko Igarashi, Fujio Oomori1963 Volume 83 Issue 8 Pages 778-780
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESS2-Amino-5-[2-(5-nitro-2-furyl) vinyl]-1, 3, 4-thiadiazole (I) was prepared by the oxidation of nitrofurylacrolein thiosemicarbazone. Eight kinds of similar-type compounds were prepared, and their antibacterial action and therapeutic effect against mice infected with Streptococcus haemolyticus were examined. I had a great effect and its effect was compared with that of sulfamethylthiadiazole (Urocydal), which is known as the urethral infection therapeutic. It was thereby learned that the nitrofuran ring had chemotherapeutic effect even in vivo.View full abstractDownload PDF (372K) -
On the Distribution Equilibrium of Isoniazide DerivativesMasayuki Nakagaki, Ken-ichi Nara1963 Volume 83 Issue 8 Pages 781-784
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDistribution coefficients of isonicotinoylhydrazone (isoniazone) of calcium pyruvate, sodium pyruvate, glucose, and sodium glucuronate between isoamyl acetate and water at 30° were determined by considering the hydrolysis equilibria of the isoniazones in both phases. For this purpose, the concentrations of INAH, isoniazones, and carbonyl compounds were measured in the aqueous and oil layers, and the distribution coefficient of each component and the equilibrium constant of the hydrolysis in both layers were calculated. It was found that the isoniazones may be classified into three types on the basis of oil/water distribution characteristics and that the calculated equilibrium constants of hydrolysis reaction in the aqueous layer coincide well with the directly measured values in aqueous solution. The distribution of isoniazone itself is so poor that the antitubercular activity of isoniazones seems to be mainly due to INAH produced by the hydrolysis reaction.View full abstractDownload PDF (479K) -
Pharmacological Action of 1, 4-Bis[(2-nethoxy-4-propylphenoxy)acetyl] piperazineTsutomu Irikura, Keigo Nishino, Noriko Ichinoseki1963 Volume 83 Issue 8 Pages 785-791
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSExaminations were made on the analgesic and related pharmacological action of 1, 4-bis[(2-methoxy-4-propylphenoxy)acetyl] piperazine (AP-2). Its analgesic action is equal to that of codeine phosphate by the pressure method and about one-half of that by the D'Amour-Smith method, being over 4 times that of sulpyrine. This analgesic action of AP-2 is not antagonized by nalorphine. Acute toxicity is low and there is no effect on the growth, fertility, blood picture, or tissue pattern of the organs by longterm administration. AP-2 markedly lowers the body temperature of albino rats and its antipyretic action on febrile rabbit is slightly stronger than that of sulpyrine. AP-2 has 1/2 to 1/4 of the antiphlogistic action of anlinopyrine and shows suppressive action of long duration on dextran edema and egg-white edema. It is synergistic with the hypnotic action of methylhexabital but has weak action of extending sleep. AP-2 does not antagonize convulsion caused by convulsion-producing agent.View full abstractDownload PDF (1012K) -
On the Reaction Product of α- or β-Naphthol with 2, 4-Dinitrophenylhydrazine in the Presence of Chloramine TMasuo Umeda1963 Volume 83 Issue 8 Pages 792-795
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSIn the presence of chloramine T, the reaction between 2, 4-dinitrophenylhydrazine, and α-, β-naphthol in acidic solution afforded the corresponding products. α-Naphthol gave red needles, m. p. 277.5°(decomp.), which showed yellowish orange coloration (λmax 460mμ) in acidic solution and blue coloration (λmax 640mμ) in alkaline medium, which is reversible of having isosbestic point at 508 mμ. The elemental analysis, UV and IR spectra of the crystals are quite identical with 4-(2, 4-dinitrophenylazo)-1-naphthol which was synthesized from the reactions of α-naphthoquinone and 2, 4-dinitrophenylhydrazine or of α-naphthol and 2, 4-dinitrophenyldiazoniumsulfate. On the other hand, β-naphthol gave reddish orange needles, m. p. 305.5°(decomp.), showing orange-yellow coloration (λmax 480mμ) in acidic solution and blue (λmax 600mμ) in alkaline medium. This coloration is reversible of having isosbestic point at 522mμ. The elemental analysis, UV and IR spectra are identical with 1-(2, 4-dinitrophenylazo)-2-naphthol which was synthesized from β-naphthol and 2, 4-dinitrophenyldiazoniumsulfate but was not identical with 2-(2, 4-dinitrophenylazo)-1-naphthol which was synthesized from β-naphthoquinone and 2, 4-dinitrophenylhydrazine. Therefore, the products in this reaction were found to be 4-(2, 4-dinitrophenylazo)-1-naphthol in the case of α-naphthol and 1-(2, 4-dinitrophenylazo)-2-naphthol from β-naphthol.View full abstractDownload PDF (594K) -
Kichitaro Takatori, Mutsuo Takashima1963 Volume 83 Issue 8 Pages 795-799
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSApplication of oxalyl chloride to 5-methoxyindole gave 5-methoxyindole-3-glyoxylyl chloride as orange-red crystals, m. p. 134°(decomp.), and application of ammonia to this chloride afforded 5-methoxyindole-3-glyoxylamide as yellow plates, m. p. 248°. The yield was almost quantitative in both reactions. Reduction of this amide with lithium aluminum hydride in a mixture of tetrahydrofuran and ether gave 5-methoxytryptamine in a good yield. Condensation of 5-methoxytryptamine and phenyl acetate by heating in tetraline or α-methylnaphthalene at 160-180° for 2 hours resulted in the formation of melatonin, obtained by Lerner and collaborators from ox pineal gland. The synthetic melatonin, obtained in a good yield, came as pale yellow leaflets, m. p. 116°, and its solution exhibited a marked yellowish green fluorescence. This substance shows absorption maximum at 277.5mμ in its ultraviolet spectrum and exhibits green by Keller's reaction and violet by van Urk's reaction, which are the specific color reactions of tryptamine series compounds.View full abstractDownload PDF (710K) -
Isolation of Dihydrosecurinine from Securinega suffruticosa (PALL.) REHDSeiichi Saito, Noboru Shigernatsu, Zen-ichi Horii1963 Volume 83 Issue 8 Pages 800-801
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSA new alkaloid, m. p. 58-60°, was isolated from Securinega suffruticosa (PALL.) REHD. The minor alkaloid was identical with dihydrosecurinine which was derived chemically from securinine, the main alkaloid of the same plant.View full abstractDownload PDF (292K) -
Itiro Yosioka, Yasuhiro Yamada1963 Volume 83 Issue 8 Pages 801-802
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSExtraction of the root of Inula helenium L. afforded, besides the known alantolactone-series compound, dammaradienyl acetate.View full abstractDownload PDF (312K) -
The Metalation Product of Dibenzo-p-dioxinShin-ichi Ueda1963 Volume 83 Issue 8 Pages 802-804
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSDibenzo-p-dioxin-dicarboxylic acid derived from the dimetalation product of dibenzo-p-dioxin (I) was proved to be dibenzo-p-dioxin-1, 6-dicarboxylic acid (IV) and this proved that the metalation took place in the 1- and 6-positions of dibenzo-p-dioxin (I).View full abstractDownload PDF (418K) -
Synthesis of Octamethyldibenzo-p-dioxinShin-ichi Ueda1963 Volume 83 Issue 8 Pages 805-807
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSOctahalodibenzo-p-dioxin (VII) and (VIII), synthesized earlier, are negative to the dibenzo-p-dioxin reaction using conc. sulfuric acid and potassium nitrate or other oxidation agents. In order to examine whether this negative coloration is due substitution of all hydrogen atoms in the benzene ring of the octahalo derivatives with halogen atoms or to insolubility of such substance in conc. sulfuric acid, 4, 9-diethyl-1, 2, 3, 6, 7, 8-hexamethoxydibenzo-p-dioxin (IX) was synthesized and its dibenzo-p-dioxin reaction was examined. In the present series of work, octamethyldibenzo-p-dioxin (V) was synthesized by the route shown in Chart 1 and this compound was found to color blue to conc. sulfuric acid and potassium nitrate. This has shown that the presence or absence of hydrogen atoms in the dibenzo-p-dioxin skeleton does not affect the dibenzo-p-dioxin reaction.View full abstractDownload PDF (549K) -
Synthesis and Antifungal Effect of 3-ChlorocoumarilaldehydeToshio Anmo, Yoshihiro Tsuruta, Shozo Ito, Katsumi Noda1963 Volume 83 Issue 8 Pages 807-810
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSVilsmer reaction of coumaranone and its 5-chloro derivative afforded 3-chlorocoumarinaldehyde and 3, 5-dichlorocoumarinaldehyde. Condensation of these coumarin-aldehyde with various amino compounds gave the derivatives listed in Table I. In vitro test of these derivatives against Trichophyton showed results summarized in Table II.View full abstractDownload PDF (520K) -
Colorimetric Determination of Morphine by 1-Nitroso-2-naphtholHiroshi Sakurai, Kazukichi Kato, Masuo Umeda, Shigeki Tsubota1963 Volume 83 Issue 8 Pages 811-814
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSWhen 1-nitroso-2-naphthol and potassium nitrate were reacted with morphine in acetic acid medium in the presence of a trace of sodium nitrite, a stable coloration was observed. This reaction was adopted to the colorlmetric determination of morphine. Morphine is able to be determined without any influence, even if five times as much codeine, thebaine, narcotine and papaverine as morphine exist, but meconic acid present in opium disturbs the determination in not less than the equi-amount.
Manipulation: one ml. of the sample (morphine hydrochloride, anhydrous, 50-400μg/ml.) was taken into 10ml. graduated cylinder, 5ml. of 60mg.% of 1-nitroso-2-naphthol in acetic acid and 2ml. of 10% potassium nitrate were added and maintain at 25° for 10 min. Then, one ml. of 20mg.% sodium nitrite was added, water was later added to make 10ml. It was shaken well and kept standing at 25° for 60 min. The optical density was measured at 530mμ. The optical density was measured at 530mμ. The blank was made with water, instead of the sample.View full abstractDownload PDF (536K) -
Colorimetric Determination of Oxymorphone by 1-Nitroso-2-naphtholKazukichi Kato, Kazuo Sato, Takeshi Tsuda1963 Volume 83 Issue 8 Pages 815-817
Published: August 25, 1963
Released on J-STAGE: February 19, 2010
JOURNAL FREE ACCESSThe colorimetric determination of oxymorphone hydrochloride with 1-nitroso-2-naphthol and potassium nitrate was examined. As an acidic reagent hydrochloric acid was preferable instead of acetic acid used in the determination of morphine. This method follows the Beer's law within the concentration of 50-300μg./ml., and an accuracy of the measurement was σ=0.58% (n=6).
Manipulation: To one ml. of the sample (contains 50-300μg./ml., as an anhydrous oxymorphine hydrochloride), 0.5ml. of 0.04% 1-nitroso-2-naphthol was shaken and 2ml. of 15% hydrochloric acid and 1ml. of sodium nitrate added 30% potassium nitrate (0.01% sodium nitrate 0.6ml.+30% potassium nitrate 100ml.) were added. It was maintained at 25° for 10 min. Later, water was added to make 5ml. and the optical density was measured at 530mμ.View full abstractDownload PDF (465K)
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